Serine periodate oxidation

Unique methods based on new principles have been developed within the past 10 years. Threonine (27,28,249) is oxidized by lead tetraacetate or periodic acid to acetaldehyde, which is determined by photometric analysis of its p-hydroxydiphenyl complex or iodometric titration of its combined bisulfite. Serine is oxidized similarly to formaldehyde, which is determined gravimetrically (207) as its dimedon (5,5-dimethyldihydro-resorcinol) derivative or photometric analysis (31) of the complex formed with Eegriwe s reagent (l,8-dihydroxynaphthalene-3,5-disulfonic acid). It appears that the data obtained for threonine and serine in various proteins by these oxidation procedures are reasonably accurate. [Block and Bolling (26) have given data on the threonine and serine content of various proteins. ]... 

Periodate Oxidation of N-Terminal Serine or Threonine Residues... 

Figure 1.107 The N-terminal aldehyde group on a peptide formed from periodate oxidation of serine or threonine residues can be conjugated with a hydrazide-containing molecule to produce a hydrazone bond.

Geoghegan, K.E, and Stroh, J.G. (1992) Site-directed conjugation of nonpeptide groups to peptides and proteins via periodate oxidation of a 2-amino alcohol. Applications to modification at N-terminal serine. Bioconjugate Chem. 3, 138-146. 

Hydrolysis of ferrirhodin with HI gives serine, glycine, alanine, ornithine and ammonia in the ratio 0.20 1.00 1.55 2.95 0.02. Alanine is not found on hydrolysis with HC1. Periodate oxidation gives cfs-5-hydroxy-3-methyl-pent-2-enoic acid, isolated as the lactone. Reduction with H2 and palladium charcoal gives hexahydroferrirhodin, identical with hexahydroferrirubin. 

This characteristic component of the phytosphingolipids gives L-serine phosphate on oxidation with permanganate and hydrolysis, followed by periodate oxidation. 

T. Kawakami, K. Akaji, S. Aimoto, Peptide bond formation mediated by 4,5-dimethoxy-2-mercaptobenzylamine after periodate oxidation of the N-terminal serine residue, Org. Lett. 2001, 3, 1403. 

AMerminal glyoxalamide Figure 4.20 Terminal serine reactive probes. Sodium periodate oxidation of W-terminal serine. 

Figure 1.106 An N-terminal serine or threonine residue can be oxidized with sodium periodate to produce an aldehyde group. The reaction can be quenched with sodium sulfite to eliminate excess periodate.

Dissolve the peptide containing an N-terminal serine or threonine group at a concentration of at least 2mg/ml in 0.04 M sodium phosphate, pH 7.0. Higher concentrations of peptides or proteins may be used without modification to the rest of the protocol, because the amount of periodate used in the reaction is in sufficient molar excess, even when low-molecular-weight peptides are being oxidized. Peptides that are initially insoluble... 

---